Basic phenolalkylether



Patented Aug. 20, 1929.

UNITED STATES l,725,136 PATENT OFFICE.

HANS HAHL, OF ELBERFELD, GERMANY, ASSIGNOR TO WINTHROP CHEMICAL COM- I PANY, INQ, OF NEW YORK, N. Y., A CORPORATION OF NEW YORK.

BASIC PHENOLALKYLETHER.

No Drawing. Application filed March 22, 1928, Serial No. 263,973, and in Germany April 11, 1927.

The present invention relates to compounds of the probable general formula:

O 1 wherein the Xs represent alkyl groups, y

represents an alkylene group, the Zs repre sent hydrogen or alkyl at least one Z being alkyl, and R represents an unsaturated aliphatic radical.

wherein Hi represents halogen, Y represents an alkylene group and the Zs represent hydrogen or alkyl, at least one Z being alkyl, 0 react upon a compound or" the general iorrnula:

Ra yea K/ it wherein the Xs represent alkyl groups and R represents an unsaturated aliphatic radical.

The new substances are mostly liquids possessing a basic odor and form neutral salts with acids which salts retain the therapeutically Valuable properties of the new products and are soluble in Water. They can be used for subcutaneous ll'lJQCtlOIl. They exhibit a pronounced action on uterus and are therefore valuable substitutes for secale cornutum.

Example: 12 parts by Weight of t-alkyl- 2.tl-climethoxy-l-phenol and 12 parts by weight of diethyl amino ethyl chloride are dissolved in parts by weight of alcohol, to which solution is added a solution of 1 5 parts by Weight of sodium in 50 parts by weight of alcohol. Heating for some time is then effected, the alcohol is distilled oif and the residue is decomposed With water. An oil separates, which is removed and fractionated. The diethyl amino ethyl ether of l-allyl-2.6-dimethoxy-l-phcnol distils at 5 mm. pressure at l46151 C. as a yellow colored oil, which has the following constitution:

CzH5 OCH2CH2N CzH5 oH=o 0-CH (4H5 forming a water-soluble hydrochloride.

Other phenols or other dialkyl-aminohald genides can be used, c. g. diniethylaminoethylehloride, et-crot-yl-Qfi-dimethoxy-l-phenol etc.

I claim:

1. As new products compounds or" the probable general formula i onto-(X04211; l i

/aHs being a yellow oil boiling at 146451 C. under a pressure of 5 mm. and forming a hydrochloride soluble in water and being a valuable substitute for secale cornutum. substantially as described.

In testimony whereof I have hereunto set my hand.

HANS HAHL.

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